As populations age, increased focus is given to the importance of enabling older people to age in place. The study reported in this paper explored the extent to which older people considered their homes and neighbourhoods to be ‘supportive’, and sought to increase understanding of the needs and experiences of older people and their expectations of future housing needs. This paper reports qualitative data from the Housing and Independent Living (HAIL) study carried out in Australia. Semi-structured interviews were conducted with 202 community-dwelling people aged 75–79 years. Interviews were transcribed, coded and analysed using computer-assisted qualitative analysis and a narrative approach to identify broad themes. Thematic analysis was used to examine and understand how occupants subjectively viewed their homes, and how they planned to adapt/modify either their activities or homes to accommodate changing needs. Six key themes emerged, namely housing choice, attachment to place, financial issues, changes to the home over time, transport, and anticipating the future. In this study, people who most strongly identified with and felt connected to their neighbours/communities had more positive perceptions of their homes and communities, and may be better able to remain in their home despite increasing disability or frailty. Housing policies and home and urban design should ensure home and neighbourhood environments are safe, accessible, promote positive associations, and are adaptable to facilitate independence and accommodate change as people age.